


If It Was To Work

by Deangirl93



Category: Supernatural
Genre: Angst, Canon Divergent, F/M, Fluff, Happy Ending, Post-Episode: s15e08 Our Father Who Aren't in Heaven, Romance, Set after S15E08, Slight Spoilers for S15E08, Smut, Vaginal Fingering, Vaginal Sex
Language: English
Status: Completed
Published: 2020-05-08
Updated: 2020-05-08
Packaged: 2021-03-03 03:13:53
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,979
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24067918
Author URL: https://archiveofourown.org/users/Deangirl93/pseuds/Deangirl93
Summary: Dean gave Sam some great advice. Sam just wishes he’d take his own advice sometimes.They had a lot on their plate with their Chuck situation, but that doesn’t mean they can’t take on an old-fashion, black and white case. That also doesn’t mean they can’t go out and celebrate a job well done afterwards.Walking into that bar and seeing you was the last thing Dean thought was going to happen.Maybe Sam’s right. Maybe he should listen to his own advice.**SET AFTER 15.08 OUR FATHER WHO AREN'T IN HEAVEN**
Relationships: Dean Winchester & You, Dean Winchester/Reader, Dean Winchester/You
Kudos: 29





	If It Was To Work

**Author's Note:**

> Hello! It's been a while since I've written anything, and this one-shot has been in my head since that episode happened. So, I thought I would write it! Let me know what you all think! :)

* * *

Some would probably say that going off to kill some vampires in Iowa while they still have their God problem would be a bad idea.

To Dean, it was the best idea Sam had that week.

He had been itching to get back to a regular, normal, non-Chuck related hunt for weeks and he was very glad to be hacking heads off vamps just outside of Des Moines.

Taking out a cloth from his back pocket, Dean walked towards the Impala as he wiped the cloth down the length of the machete to get the blood off. He dropped the machete into the weapons box, just as Sam came up behind him and did the same. Dean shut the trunk and walked over to the driver’s side, getting in and starting the engine.

“I don’t know about you, but I could go for a cool one” Dean smirked, as the radio started.

Sam nodded. “You know what, let’s do it.”

Dean frowned. “Seriously?”

“Yeah, I mean we haven’t done a victory beer at a bar in a while, so why not?” Sam shrugged.

“Okay.” Dean said, looking between Sam and the road. “Better take this opportunity now before you change your mind.”

* * *

After driving for about 15 minutes, Dean spotted a roadside bar. He pulled the Impala up into an empty spot, before shutting the engine off. He got out of the car, as Sam followed behind him.

“You grab a spot, I’ll get the beers” Sam said, as he took in the large gathering within the bar.

Dean looked around the bar, taking in his surroundings. They hadn’t done this in a long time, and he was glad that they didn’t have to get back to the Bunker straight away. No one had any leads on Chuck, so they could take a day if they wanted to. At this point they needed to. As his eyes roamed over the patrons, they stopped on one person in particular.

She leaned over the pool table, lining up the shot, giving him a great view of her ass in the dark blue jeans that she wore. Round, perky and irresistible. Perfect. As she stood from taking the shot, Dean caught a glimpse of the tattoo she had on her right arm; a sleeve of vines and flowers. She laughed, as the two burly men they were playing with forked over a roll of cash each. The girl had confidence. Dean smirked, already taking out some cash to buy her a drink. Something about her felt familiar, though, as he continued to admire her.

When she turned away from her friend and faced the rest of the bar, it hit him like a fucking Mack Truck. A flood of memories flashed through his mind, all at once, knocking the wind out of him.

Y/N. Y/N was here. In the same bar as him. After all these years of never having run into each other, not even on a hunt, and here she was.

Damn it. This had to be Chuck’s doing, right?

He suddenly heard a snapping sound and saw something waving in front of his face. He shook his head and looked away, facing Sam. His brother was wide-eyed and confused, his forehead creased as he looked at him.

“Dean, where the hell were you?” he asked.

Dean shook his head again, lifting the beer to his lips and taking a large gulp from it. “N-nothing. I mean, nowhere. Nothing. Shut up.”

Sam raised an eyebrow, bewildered by Dean’s sudden odd behaviour. “You okay?”

“Yeah, I just-” Dean started to answer Sam but when he looked up, he saw that Y/N was walking towards the bar.

She was wearing a tight black Led Zeppelin t-shirt, and her Y/C/H flowing behind her as she walked. However, much like him, she took in her surroundings and stopped in her tracks when she saw him. Sam saw Dean go completely still and wondered what was happening. He turned around and knew straight away what was going on. No wonder he was acting strangely. Dean slowly got up from the stool at their high top, leaving his drink behind. As he hesitantly walked closer to Y/N, her eyes widened in shock. He was just a few inches away from her when he took in her features. She hadn’t changed; she was still as beautiful as ever.

Y/N took him in. How was it possible that the man became more attractive with age? She looked past him at Sam, who gave her a small smile. She couldn’t believe that in all the years since she and Dean parted ways, she would be seeing them again now and in the most random of bars.

“H-hi” she squeaked out, as she moved closer to Dean.

Dean nodded. “Hey.”

She brushed her knuckles together, as she looked around the room. She was trying to avoid looking at him too long, for fear that she might burst into tears.

“How are you?” she asked, only glancing at him before looking away again.

A sad smile crossed Dean’s face when he realised what she was doing. She was forgetting how well he knew her.

“Have I really changed that much that you can’t look at me?” he said, in the most light-hearted manner he could muster up, but it still held a sadness behind it.

She finally looked up at him. “You haven’t changed a bit.”

“You’d be surprised” Dean grimaced, wishing he had brought his drink over with him.

Everything else in that bar faded into the background as Dean and Y/N continued to look at each other. A range of thoughts and emotions flooded Dean’s mind as he thought back on how they had left things the last time they were together. There was so much about that night that he regretted, the most painful of which he knew was something neither of them had gotten over. It was the greatest regret of his life; letting her go. Pushing her away. What he didn’t know was that she completely understood why he did what did. She always understood.

Y/N looked back at her friend who was still preoccupied by the men they were playing pool with. She turned back to Dean and knew she had a couple of options here. She either walked away and went back to her friend, forgetting about him completely. Or… she asked him to have a drink with her, for old times’ sake. She took a deep breath, ready to ask him and possibly open herself up to being heartbroken again.

“Hey, you wanna grab a drink with me and Sammy?” Dean asked, beating her to it. The same thoughts had been running through his head; about whether or not to ask her.

She smiled properly this time, a full wattage smile that reached her shining eyes. “I’d love that.”

Y/N walked over with Dean to their table and smiled at Sam. Sam immediately got up from his seat and hugged her, causing her to laugh.

“I swear you got bigger somehow” she laughed.

“How are you?” he asked, smiling.

“I’m good” she said, simply. “Honestly can’t complain. I know you two have it worse.”

“What? You been keeping tabs on us?” Dean asked, intrigued as to whether she was or not.

“Not really, but… Garth talks. A lot” she replied, laughing again.

Dean scoffed as he smirked. “Figures.”

They all proceeded to catch up on everything from the past years. Y/N told them how she now had a place in town, somewhere to come back to after a hunt. Sam told her about the Bunker and she was suddenly giddy.

“Oh man, I gotta see it” she smiled.

“Yeah, first time we got there… couldn’t really believe that it was real” Sam said, smiling too.

Dean smirked as he watched Y/N. “You should, you know? See it, I mean. You should uh… You should come over some time.”

Y/N looked at him and smiled softly. “I will.”

Sam looked between Dean and Y/N. He remembered Dean telling him about what happened between them and knew there was a lot of things that were left unfinished between them.

“You know, I’m not feeling too great” Sam said, getting up from his seat. “I’m going to get a cab, head back to our motel. Leave you two to catch up.”

Dean glared at Sam while Y/N wasn’t looking. He knew what he was doing.

“Oh okay, well it was good to see you” she smiled, as she hugged him again.

“You too” Sam said.

As he moved behind her, Sam turned around and gestured to her. Getting Dean’s attention, he mouthed “talk” before he gave Dean a knowing smile and walked away. Dean shook his head but quickly turned back to Y/N before she noticed the silent conversation between him and his brother.

“Another round?” he asked.

“Sure” she replied.

* * *

Y/N and Dean sat across from each other, each of them had two empty beer bottles in front of them. They had both moved onto whiskey. Dean brought his glass to his lips, taking a large sip. Y/N turned the glass around in her hands, watching the amber liquid move around.

“Never in a million years did I think I’d see you again” she laughed, the sound of it somewhere between sincere and bitter. “I thought you and Sam were so good at hiding… I’d never run into you.”

Dean huffed. “Small world, I guess.”

She nodded and smiled sadly but didn’t say anything else.

“Listen, Y/N-” Dean started but she placed her hand on top of his to stop him. He looked at her and wondered what was wrong but was confused when she smiled at him.

“Dean, I know you’re about to apologise and you shouldn’t. You didn’t do anything wrong” she said.

“Didn’t do anything wrong? Are you kidding me? I left without even saying goodbye. All I gave you was a fucking note saying I had to go, and I was sorry” he said, his voice angry but lowered so no one heard them.

“Don’t you think I knew why? Dean, I knew you had to go back with your dad. I knew you would do anything for him, how important your family is to you. I get it, Dean. I always have. I don’t hold any of it against you, I don’t blame you for what you did. I never have” she explained, tightening her hold on his hand.

Dean looked up at her, his expression sad and yet bewildered by what she just said. She got it, why he had to leave. She understood.

He suddenly remembered the advice he gave Sam recently about Eileen.

_She gets it, you know? She gets us, she gets the life._

It was with the same with Y/N.

_If it was to work…_

Could it work again? For them? Could they go back to what they were with everything that was going on with Chuck?

_You don’t ever think about something? You know, with a hunter? Somebody who understands the life?_

Sam had said that to him once. When he would find himself thinking about Y/N over the years, he always thought about what Sam had said.

Y/N gripped his hand tighter, smiling as she looked down at their hands intertwined. She stroked her thumb over his knuckles, thinking back on all the times she had done it all those years ago.

“I missed you” she said, looking up at him.

Dean looked into her eyes. He could see what she was feeling in that moment because he felt the same. He had a decision to make. Let go of her hand, get in the Impala and drive away, leaving her behind. Or take her hand, go back to her place and pick up where they left off. Option 2 was tempting but he was scared. Scared of what might happen to her if he did. Then the words he said to Sam repeated themselves in his mind. He had to try.

Dean picked up his drink and gulped down the whiskey in one hit. Y/N did the same, knowing what was thinking and being on the same page as him, instantly. He took out a few bills from his wallet and put them under his glass, before taking her hand in his. He led her out of the bar and over to the Impala. Opening the door for her, she sat inside before he walked over to the driver’s side. Getting in behind the wheel, he started up the engine.

“So, where to?” he asked.

She smiled as he turned the radio on. Zeppelin. Just like old times. “Take a left at the exit.”

Dean pulled out of the parking lot and followed Y/N’s directions all the way to her house. When they arrived, he parked outside. It was a small, quaint one-storey, enough for her and maybe even someone else to live in. They got out of the car and he followed behind her as she guided him inside. It was spacious and decorated simply, yet it wasn’t empty by any means. The lounge flowed into the kitchen which had a door to the backyard and outdoor furnishings.

“Nice place” Dean said, looking around.

“It was my parents. When dad died after the ghoul hunt, he gave it to me, but I started hunting instead. When I realised I needed a safe place to come back to, I came back here” she explained.

Y/N walked closer to Dean. “You want another drink?”

He shook his head as she stood in front of him, close enough to smell her perfume.

“No” he replied, simply.

Dean pulled her closer, before he leaned down and pressed his lips to hers. She kissed him back, instantly. She wrapped her arms around his neck as his came around her waist. He lifted her up and she wrapped her legs around his waist, their lips still connected. He felt the same, like nothing had changed, and yet it somehow felt new.

She pulled away from the kiss but still kept her lips against his. “Down the hall, on the right.”

She leaned down to press her lips to neck, as he carried her to the bedroom. He was slightly distracted by her lips as he stumbled down the hallway but made it to the room without crashing into things.

She lowered herself from him, her feet firmly on the floor. They didn’t waste any time, as they kissed heatedly and began to remove their clothes. Dean pulled away to take her in as she stripped down to red bra and panties. She was as beautiful as the first time he saw her.

“Fuck” he groaned, as he leaned in and began kissing her neck.

She took his shirt in her hands and pushed it off, only pulling away from him to lift his black shirt over his head.

“Dean” she moaned as her hands roamed his chest.

Dean gently placed his hand behind her head, until she laid down on her back. He sat up to pull her bra off, and leaned in to place kisses along her breasts. His hand wandered down her body, his fingers feeling how wet she already was through her panties. He wanted her so badly, even after all this time apart. He missed her.

His hands trailed her body, feeling her smooth skin against his calloused hands. She whimpered, feeling his rough yet light, soothing touch. She closed her eyes as she thought about how they were in the past, and how much she still wanted him. So much time had passed since they were last together like this, but he still remembered the right pressure and movements that drove her crazy. He pulled her panties down her legs and slowly ran his fingers along her pussy.

“Dean” she sighed, in a needy whisper. She pushed herself up on her elbows and cupped his cheek in her hand. “Can we… can we do that later? I just…”

Dean smirked and leaned forward, nudging his nose against hers. “What do you want, sweetheart?”

She bit her lip as she looked into his eyes, just as lust blown as hers. “I want you inside me.”

He leaned forward and kissed her, passionately, before he shifted back. He wasn’t about to waste any more time with her.

He quickly pushed his boxers down before he moved closer to her. Y/N pulled him as close as she could to her, wrapping her arms around his neck as he settled himself between her legs. He pressed his lips against hers, as his hands moved her legs to wrap around his waist, trying to get even closer to her if that was possible. She reached down between their bodies and took his length in her hand, holding it near her entrance. Dean moved his hips forward as he looked down at her, his cock slowly pressed into her. He watched as her eyes fluttered closed, a small smile spread across her face. When he was fully inside her, he waited. He wanted to do this right and not rush things. Apparently Y/N had other ideas though, as she combed her fingers through his hair roughly, and pulled him in with her legs.

“Dean” she gasped against his lips. “Please move.”

Dean chuckled softly, kissing her once. “Someone’s impatient.”

She gripped his hair tighter and he groaned at the slight sting of pain. He glared down at her playfully as she winked, her eyes glinting with mischief. He shook his head and smirked, leaning down to kiss her once again.

Dean pushed his hips forward and then back. He set a slow pace, thrusting carefully and taking his time. She leaned up and kissed his neck, biting his collar bone as her arms wrapped tighter around him. They looked into each other’s eyes, seeing all the years of longing for each other and how much they still loved each other.

“Dean” she moaned. “Harder.”

Dean wrapped his arms around her back and sat up. He leaned back and sat her in his lap, looking right into her eyes and their arms came around each other. She moaned into his mouth as his lips captured hers, her hands in his hair as her hips rocked against his. His left hand wandered into her hair as his right held onto her hip, his fingers pressing into her flesh.

“Fuck” he groaned, as her hips came down hard, repeatedly.

“Dean… I love you” she said, a hitch in her voice.

His hips begin to rock harder against her, as he pulled her in even closer. He kissed her fiercely, lightly biting her lip.

“Dean, I… oh my God” she moaned loudly, as she kissed her neck, the spot that always drove her crazy.

“Fuck, sweetheart” he huffed. “You feel so damn good.”

“Dean, I… I’m close” she gasped.

Dean could feel it. Her hips started to move faster, stutter slightly as she became overwhelmed with what she was feeling.

“Let go for me, Y/N” he said, looking up at her.

“Dean, I…” she started but cut herself off as she moaned loudly.

Y/N’s eyes shut tightly, as she moaned his name repeatedly through her climax. Dean’s hips moved faster and harder, as he feels his own release. Y/N placed her hands on his neck, as her thumbs ran along his jaw.

“Dean, baby” she moaned sweetly, as she smiled at him. “Cum for me, Dean. Cum inside me.”

“Fuck, Y/N” he grunted as he came, spilling his seed inside her.

He rode out his climax, resting his forehead against her chest. Y/N held him close, her hands in his hair, lightly massaging his scalp.

They came down from their high, breathing heavily. Dean lifted his head and looked up at her, his hand cupping her cheek and bringing her closer. Their lips met in a soft kiss, once, twice. Dean pulled away and looked at her again.

“I love you” he whispered, his breath still laboured from their love making.

Dean slowly pulled out of her, turned and laid down on his back. Y/N laid down next to him and pushed herself closer. He wrapped his arm around her as she laid her head on his chest and hooked her leg around his. They laid there in silence for a while, as they enjoyed the quiet and basked in the afterglow. Dean took a deep breath, trying to figure out what he was going to say next. How he was going to say what he wanted to since they got to her apartment.

“Penny for your thoughts?” she asked, breaking the silence first.

Dean huffed a laugh. Of course, she knew that he wanted to say something.

He took another deep breath. “What would you say… if I said that I… if I said that I wanted to start things up again?” he asked, ripping off the Band-Aid.

Y/N turned and leaned her chin on his chest. Her eyebrows furrowed as she didn’t say anything for a few moments.

“What do you mean?” she asked him.

Dean brushed his hand down her arm, absentmindedly. “I mean that we hunt, together, and then we came back here… or the Bunker… together.”

She smiled softly as she thought about what he meant.

“Some things that have happened recently, they’re… they’re making me think differently about this life. About my life. I just know that now that we’re back here…” Dean explained, taking her hand in his. “I’m not ready to give it up again.”

She sighed as she leaned in and kissed his hand. “Me neither.”

“I know I’m risking everything again, doing this with you. I mean, we’re on God’s radar, and he could strike down at any minute but…” Dean started but stopped when she cut him off with her lips. She kissed him hard, pulling away and leaving him breathless.

“We can do it, Dean. Things are different now… scarier, yeah, sure but… I get it. I know what your life is and what it could mean, I know that joining you means I won’t be a regular, running-after-a-normal-monster hunter anymore. I know it and… I don’t care. Despite everything, despite whatever gets thrown at us… I know we can make it work” she said, as she shifted forward and leaned her forehead against his.

Dean smirked. _She gets it. She gets the life._ “So… we’re really doing this?”

She grinned back. “Yeah. We are.”

Dean leaned in and kissed her, passionately. He slowly rolled her onto her back, the kiss growing and becoming more intense. They both knew the risks, hell, they knew they could die at any minute, but as long as they had each other they had something more to fight for. The years of missing each other and now finding each other again, it would all be worth it when they got out of this alive. He was determined. They would find a way to get rid of Chuck, they would find a way to live a comfortable life, and when that happened, he wanted Y/N by his side.

* * *

The next morning, after the sun had risen and they made love once again, Dean made her breakfast. They ate and laughed together. Dean answered a call from Sam about another hunt he found. Y/N packed up her duffle bag and placed it next to Dean’s in the Impala’s trunk. They smiled at each other as she sat next to him, listening to classic tunes as they went to meet up with Sam and go off on the next hunt.

Together.

**Author's Note:**

> Thanks for reading! Hope you all enjoyed! :)


End file.
